Woodbury Real Estate

Welcome to Woodbury, Connecticut, a charming town nestled in the heart of Litchfield County. Known for its picturesque landscapes and rich history, Woodbury offers a unique blend of small-town charm and modern amenities. With a population of just over 9,000 residents, this close-knit community is perfect for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

Woodbury is renowned for its beautiful countryside, featuring rolling hills, lush greenery, and scenic views that change with the seasons. The town is dotted with historic homes and buildings, reflecting its deep-rooted heritage. Outdoor enthusiasts will find plenty to love, with numerous parks, hiking trails, and recreational areas, including the stunning Hollow Park, which offers a variety of activities from picnicking to sports.

The town’s vibrant community spirit is evident in its local events, farmers' markets, and artisanal shops, where residents come together to support small businesses and celebrate local culture. Woodbury is also home to a range of dining options, from cozy cafes to gourmet restaurants, ensuring that there’s something to satisfy every palate.

Education is a priority in Woodbury, with excellent schools and a commitment to fostering a supportive learning environment for children. The town's convenient location provides easy access to nearby cities, making it an ideal spot for commuters who desire a serene living environment without sacrificing convenience.

Whether you're looking to buy your first home, retire in tranquility, or simply explore a beautiful town, Woodbury, CT, is a hidden gem waiting to be discovered. Come experience the warmth and charm of this idyllic New England community!

Newest Listings in Woodbury

$329,900

3 Beds ⋅ 2 Baths ⋅ 24195376 MLS ⋅ Woodbury Place BLDG.

Move right into this beautifully updated 3-bedroom, 2-bath townhouse offering style, comfort, and low-maintenance living. Gleaming hardwood floors flow throughout the home, complemented by vaulted ceilings, a skylight providing abundant natural light. The updated galley kitchen features tasteful tile backsplash and efficient design, opening to a spacious living and dining area highlighted by a cozy electric fireplace and ceiling fan. Sliding glass doors lead to a private patio with peaceful ideal setting for morning coffee, birdwatching, entertaining or simply relaxing. A convenient outdoor storage shed adds extra functionality. The main level offers two generously sized bedrooms with ample closet space, a full bath a including washer and dryer closet. Upstairs, a dramatic open loft overlooks the living area and leads to a spacious primary suite featuring a unique barn-door closet, walk-in closet, and an updated full custom tiled shower with double vanity, skylight and elegant cabinetry. Wake up to seasonal lake views from the primary bedroom suite. Central Air & updated blown in insulation are just some additional perks. A detached two-car garage provides additional storage and convenience along with an additional dedicated parking space. Ideally located with easy access to I-84, charming shops, a plethora of dining and so much that Southbury and Woodbury have to offer. This exceptional home combines comfort, convenience, and scenic surroundings in desirable Woodbury Place.

22 Woodbury Pl Unit 22, Woodbury

$1,395,000

3 Beds ⋅ 3 Baths ⋅ 24192284 MLS

Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

509 Weekeepeemee Rd, Woodbury

$525,000

3 Beds ⋅ 2 Baths ⋅ 24189460 MLS

Well maintained and updated Raised Ranch 3 bedroom 1.5 bathrooms home ready to move in! Open concept living room/dining room and kitchen that opens on to a gorgeous 12'x30' deck overlooking a beautiful fenced in backyard in the woods make for a very private setting. This home has all new windows, a newly updated kitchen with stainless steel appliances and granite countertops, finished lower-level ideal for home office or living space with plenty of natural light, windows and recessed lighting. Cutting edge solar panels save on electric bill! Conveniently located close to all amenities, shopping, dining, and major highways. Enjoy all that Woodbury has to offer - rated best town by Yankee Magazine. "Sold as is condition" a must see!

212 Upper Grassy Hill, Woodbury

$819,900

3 Beds ⋅ 3 Baths ⋅ 24192675 MLS

Welcome to 17 Curtiss Road! This one-of-a-kind 1.8-acre property offers the perfect blend of historic charm and modern convenience, featuring a well-maintained 1900 single-family home, an attached 2-car garage, and an impressive detached 24' x 50' heated 3-car garage built in 2022. Step inside the home and be welcomed by a charming foyer leading to wide-board hardwood floors and six mini-split systems (2019) that provide efficient heating and cooling throughout. The inviting living room features custom built-ins and flows seamlessly into the spacious kitchen, complete with stainless steel appliances, ample cabinetry, recessed lighting, a pantry closet, and basement access. Just off the kitchen is an updated half bath with tile flooring and laundry hookups. Off the kitchen the elegant dining room offers crown molding and plenty of space for entertaining. Completing the main level is a spacious primary suite with double closets and a beautifully updated full bath boasting heated tile floors, a skylight, recessed lighting, chair rail molding, and a linen closet. An adjoining den with custom built-ins provides the perfect space for a home office, reading room, etc. Upstairs, you'll find two generously sized bedrooms, each with walk-in closets and shared access to a Jack-and-Jill bathroom featuring a dual-sink marble vanity. The basement includes 200-amp electrical service, Energy Star hot water heater, well tank (2018), and additional laundry hookups. Outside, enjoy

17 Curtiss Rd, Woodbury

$349,500

3 Beds ⋅ 3 Baths ⋅ 24191489 MLS ⋅ Woodlake BLDG.

Welcome to Woodlake! Move right in and enjoy the space, comfort, and lifestyle this beautifully maintained 3-bedroom, 2.5-bath townhouse has to offer. The light-filled and flexible floor plan includes spacious main-level living, 2 generous upstairs bedrooms, and a huge finished walkout lower level with an additional room perfect for a home office, gym, or hobby space. Updates and improvements are too numerous to mention. Highlights include an electric fireplace insert, a cozy wood stove, and a beautifully renovated upstairs bath with a jetted tub. (Ask your Realtor for a full list.) A large unfinished basement area provides abundant storage. Outside, enjoy a meal or coffee on your private deck, and you'll even enjoy the short scenic walk from your car (1 carport and 1 assigned parking spot!) to your front door. Life at Woodlake is about more than the home. Enjoy walking trails, a tranquil pond for canoeing, picnic areas, a playground, and a peaceful setting surrounded by nature. Just minutes away, historic Woodbury offers exceptional restaurants, charming shops, antique stores, New Morning Market, Flanders Nature Center, Earth Tones Native Plant Nursery, and easy access to I-84, giving you the perfect blend of country charm and everyday convenience. As an added bonus, Woodlake is FHA-approved and pet-friendly. Schedule your private showing today and experience everything Woodlake has to offer.

4 Alder Court, Unit 4, Woodbury

$398,000

3 Beds ⋅ 2 Baths ⋅ 24186179 MLS

Warm and welcoming, this vintage home with a classic rocking chair front porch is ideally located within walking distance of Woodbury's town center. Beautifully maintained, it blends timeless character with thoughtful updates throughout. A gracious foyer with hardwood floors and a wall of closets provides exceptional storage. The living room features hardwood floors, built-in shelving, and an electric fireplace, while the dining room showcases a classic built-in cupboard. The updated country kitchen offers Vermont soapstone countertops and new flooring, and a convenient main-level laundry room with a half bath completes the first floor. Upstairs are three bedrooms and a full bath. Energy-efficient improvements include newer windows and doors, along with individual thermostats in every room for personalized comfort. An enclosed rear porch provides the perfect mudroom or everyday entry. Outside, the level backyard has been transformed into a park-like retreat with a new patio, attractive landscaping, and plenty of space for entertaining, gardening, or simply relaxing. A shed provides additional outdoor storage. Located in Woodbury, named Reader's Digest's "Most Charming Small Town" three times, this home offers easy access to restaurants, galleries, cultural venues, day spas, hiking trails, ski areas, wineries, and equestrian facilities. Approximately 90 minutes from Manhattan, it offers the perfect blend of small-town charm and convenience. Seller reviewing offers.

9 Spring St, Woodbury

$525,000

3 Beds ⋅ 2 Baths ⋅ 24191493 MLS

Classic 1800s vintage Colonial in Connecticut's most charming town! Located within a short drive of all major conveniences, area private/public schools and parks, this three bedroom, two bath home has something for everyone! Situated on a beautifully level lot, enjoy your 1.55 acres by throwing the ball around, entertaining on your slate side patio or terrace area. The backyard barn, named the "Carriage House", is a unique feature of the property that is just waiting for you to cultivate your favorite hobby. On the main level of the home you will find a spacious country kitchen with hook up for a woodstove. The formal dining room can fit the relatives for the upcoming holiday season, and the formal living room, with center fireplace, beams with natural light! Rounding out the first floor is a study with custom-built bookcases and a full bath off the kitchen. Upstairs are spacious bedrooms, a full bath with clawfoot tub, and a bonus room, currently used as another bedroom. Lastly, the walk up attic is fully floored and highly functional for your storage needs or other use. Come and appreciate how this property reflects Woodbury's 19th century antique flair!

520 Washington Rd, Woodbury

$250,000

24192651 MLS

An exceptional opportunity to own 76.9 +/- acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of this 14.9-acre parcel and the adjoining 62-acre parcel (MLS #24192209). Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, and open fields, creating endless possibilities for the next owner. Whether you're seeking a private country estate, equestrian property, family compound, recreational retreat, hunting property, or a prime development opportunity, this expansive acreage provides the flexibility to bring your vision to life. Surrounded by the natural beauty of Woodbury while offering convenient access to local amenities, this is a truly remarkable opportunity to invest in one of Litchfield County's most sought-after communities. A rare offering where privacy, scenic landscapes, and future potential come together.

Hoop Pole Hill, Woodbury

$1,000,000

24192209 MLS

An exceptional opportunity to own 76.9 acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of 14.9-acre parcel (MLS# 24192651) and this adjoining 62-acre parcel Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, and open fields, creating endless possibilities for the next owner. Whether you're seeking a private country estate, equestrian property, family compound, recreational retreat, hunting property, or a prime development opportunity, this expansive acreage provides the flexibility to bring your vision to life. Surrounded by the natural beauty of Woodbury while offering convenient access to local amenities, this is a truly remarkable opportunity to invest in one of Litchfield County's most sought-after communities. A rare offering where privacy, scenic landscapes, and future potential come together.

245 Hoop Pole Hill Rd, Woodbury

$1,100,000

4 Beds ⋅ 4 Baths ⋅ 24192457 MLS

Spacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of living space, including a walk-out lower level that is well suited for an in-law suite or au pair quarters. The main level features wood floors, formal living and dining rooms, an eat-in kitchen, a bedroom, a full bath, and a family room with a fireplace that opens to an oversized deck. Upstairs, you'll find three bedrooms, a full bath, and a spacious primary suite with a spa-like bath and loft area. The walk-out lower level includes three finished rooms plus a full bath, offering flexible space for guests, extended living, recreation, or work-from-home needs. The private backyard is surrounded by trees and accented with perennial gardens. NEW Roof June 2026. Located in Woodbury-one of Connecticut's most beloved small towns-the home is close to charming shops, antique stores, coffee shops, and restaurants, all just about 90 minutes from New York City.

16 Gate Post Ln, Woodbury

$649,900

4 Beds ⋅ 3 Baths ⋅ 24192145 MLS

Exceptional opportunity to renovate and create your dream country estate on 12.69 private acres in the heart of Woodbury. Privately sited along a quiet country road with seasonal long views, this 2,972 sq. ft. contemporary offers an outstanding combination of acreage, privacy, and potential rarely found at this price point. Designed for comfortable living, the home features a dramatic sunken living room with soaring vaulted ceilings, a fireplace, and walls of windows overlooking the surrounding landscape. The main level includes a spacious primary suite, private office, butler's pantry, and access to expansive decks that invite outdoor entertaining. Upstairs are 3 additional bedrooms and an open den, while the unfinished walk-out lower level offers endless possibilities for future living space. The property's 12.69 acres provide a beautiful backdrop with open land, mature trees, and a four-stall barn, offering flexibility for a variety of country lifestyles. Priced to reflect the opportunity for renovation and updating, this is an exceptional chance for investors, builders, or buyers looking to customize a solidly built home in one of Woodbury's most desirable locations. With great bones, an outstanding setting, and significant upside potential, this property is ready for its next chapter. Sold as is.

348 Hoop Pole Hill Rd, Woodbury

$699,000

3 Beds ⋅ 3 Baths ⋅ 24190540 MLS

Charming and full of character, this beautifully maintained three-bedroom Cape offers the perfect blend of comfort, warmth, and convenience in the heart of Woodbury. Set on a picturesque property with mature perennial gardens and a fenced-in yard, the home feels peaceful and private while being just a two-minute walk from downtown shops, restaurants, the library, schools, community center, and nearby hiking trails. Inside, hardwood floors and abundant natural light create a warm and inviting atmosphere. The welcoming living room features a fireplace, while the bright south-facing sunroom provides a relaxing space to enjoy throughout the day. The dining room includes a charming corner cupboard that adds timeless New England character. The finished lower level offers flexible space for exercise, hobbies, or creative pursuits and includes a sauna, shower, and fully equipped darkroom. Additional highlights include a two-car garage and beautifully landscaped outdoor spaces. A rare opportunity to enjoy distinctive features, exceptional charm, and an ideal in-town location in one of Litchfield County's most desirable communities.

31 Mountain Rd, Woodbury

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